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Related Experiment Videos

Th-C60F24.

Nadezhda I Denisenko1, Sergey I Troyanov, Alexey A Popov

  • 1Chemistry Department, Moscow State University, Moscow 119992, Russia.

Journal of the American Chemical Society
|February 12, 2004
PubMed
Summary

Researchers synthesized a novel fluorofullerene, Th-C60F24, through regioselective fluorination. This compound, featuring a unique noncontiguous fluorine pattern, exhibits kinetic stability despite less stable isomers.

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Area of Science:

  • Fullerene Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Fullerenes are carbon allotropes with unique electronic properties.
  • Fluorination of fullerenes can significantly alter their chemical and physical characteristics.
  • Developing selective synthetic routes for fluorinated fullerenes is crucial for new material applications.

Purpose of the Study:

  • To synthesize and characterize a novel fluorofullerene derivative, Th-C60F24.
  • To investigate the structural and electronic properties of Th-C60F24.
  • To assess the kinetic stability of the synthesized fluorofullerene.

Main Methods:

  • Regioselective fluorination of Th-C60Br24 using Xenon difluoride (XeF2) in anhydrous Hydrogen Fluoride (HF).
  • Characterization using Electron Ionization (EI) and Electrospray Ionization (ESI) mass spectrometry.

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  • Spectroscopic analysis including 19F NMR, 13C NMR, and Fourier-Transform Infrared (FTIR) spectroscopy.
  • Density Functional Theory (DFT) calculations to determine isomer stability.

    • Main Results:

    • Successful synthesis of Th-C60F24, isostructural with the precursor Th-C60Br24.
    • Characterization confirmed the presence of 24 fluorine atoms with a noncontiguous pattern on sp3 hybridized carbon atoms.
    • Spectroscopic data (NMR, FTIR) provided detailed structural information.
    • DFT calculations indicated that Th-C60F24 is a kinetically stable isomer, despite thermodynamically more stable alternatives.

    Conclusions:

    • Th-C60F24 represents the first fluorofullerene with a noncontiguous pattern of F-bearing sp3 carbon atoms.
    • The compound demonstrates significant kinetic stability, suggesting potential for controlled synthesis and application.
    • This work expands the scope of synthetic fluorofullerene chemistry and provides insights into fullerene functionalization.